Question: For how many ordered pairs of positive integers $(x,y),$ with $y<x\le 100,$ are both $\frac xy$ and $\frac{x+1}{y+1}$ integers?

Since $y|x$, $y+1|x+1$, then $\text{gcd}\,(y,x)=y$ (the bars indicate divisibility) and $\text{gcd}\,(y+1,x+1)=y+1$. By the Euclidean algorithm, these can be rewritten respectively as $\text{gcd}\,(y,x-y)=y$ and $\text{gcd}\, (y+1,x-y)=y+1$, which implies that both $y,y+1 | x-y$. Also, as $\text{gcd}\,(y,y+1) = 1$, it follows that $y(y+1)|x-y$. [1]
Thus, for a given value of $y$, we need the number of multiples of $y(y+1)$ from $0$ to $100-y$ (as $x \le 100$). It follows that there are $\left\lfloor\frac{100-y}{y(y+1)} \right\rfloor$ satisfactory positive integers for all integers $y \le 100$. The answer is
\[\sum_{y=1}^{99} \left\lfloor\frac{100-y}{y(y+1)} \right\rfloor = 49 + 16 + 8 + 4 + 3 + 2 + 1 + 1 + 1 = \boxed{85}.\]